I will be staying in Cortona 7/4-7/14 and am looking for information on the best ways to do day trips from there to other hill towns. Thanks for any advice.
Cortona is pretty, but that's a long stay in one place. Are you with or without a car? Does your budget include wine tastings or fine dining? What are your stops before and after Cortona?
We loved Cortona and stayed for 8 days, wishing we had planned for more. I am assuming you are going to have a car? If not, I would encourage you to rent one for your time there. The train station is pretty far from the main town. I'm not sure what the bus situation is though so perhaps others could speak to that option. With our car we did day trips to Montalcino/Montelpulciano (same day), Florence (twice!), Assisi/Deruta (same day). There are so many other towns you could visit in addition or instead of those I listed. As a side note, we thought the gelato in Cortona (I think it's called Snoopy Gelato) was some of the best we had in our whole month in Italy. The town square in the evening and at night is simply entrancing. Enjoy your time in this lovely little village!
As others have indicated you will need to negotiate between Cortona proper and the train station Camucia Cortona which is down the hill.
Some train station bus information is lower on this page: https://www.cortonamia.com/en/how-to-reach-cortona/
The good news is that in Cortona you are closer to places in Tuscany and Umbria that are often too far from places like Siena to visit as day trips. On the train you can easily reach Arezzo, Chuisi, Perugia, Spello and the lakeside of Lago Trasimeno. You are close to the famous southern Tuscan hilltowns like Montepulciano and Pienza but they are difficult to reach via public transport.
Sounds like a good time, have a great trip,
=Tod